High Maintenance creators on season 3’s ‘tonal shifts’ and guest stars — including an Obama impersonator

HBO’s underrated gem High Maintenance is hard to define. It’s billed as a comedy, sure, with the only central-ish character being a chill weed dealer, but it’s also structured in anthology form, with each episode diving into all sorts of scenarios — some humorous, some dramatic, all thoughtfully made. The slice-of-life-in-New-York approach that began back when the show was a web series has evolved and now, in its third season on the premium cable network, High Maintenance continues to transform.

Creators Katja Blichfeld and Ben Sinclair (who stars as the weed-dealing Guy) have seen the show through personal ups and downs while crafting episodes that are both timely and timeless. For the third season, they continue to try new approaches to the foundation they’ve built. The pair chatted with EW about crafting season 3.

ENTERTAINMENT WEEKLY: The season opens with a pretty Guy-heavy episode. Why’d you want to pick up with him as the focus this time? Should we be expecting him to be a more prominent character?

KATJA BLICHFELD: Every season we do struggle with how much or how little to show of that character. We like the keeping-you-guessing thing that we’ve got going, but it’s a fine line to toe. Every time we pull back a layer, we get a good response to it, and then we’re like, “Oh, should we give him a little bit more?”

BEN SINCLAIR: Do you think we need to back off?

No, not at all! Just wondering what your take is on it.

BLICHFELD: [Laughs] You obviously hit a thing that we’ve been talking about, not like a nerve, but a thing where we’re all like, “Huh.”

What were your goals going into this season, and how did they differ from previous ones?

SINCLAIR: For me as a showrunner and creator, my goal was to let the community that has rallied around this show take care of it more. There was a lot of, for me, letting go and just learning. Let the help help you — not that they’re the help.

BLICHFELD: Accept help, yes. And for me, same. The show could never continue being what it was once upon a time — just me, Ben, and [producer] Russell [Gregory] and a few friends making this thing. It had to grow to be sustainable, so it continues to be this letting go process and trusting that we’ve set something up that can withstand changes and keep growing, and also accept that it’s fine if it’s different.

There are certainly some differences in this season. Episode 2 has this horror sequence that felt very new.

BLICHFELD: Yeah! We’re trying some stuff out this season. We definitely have some tonal shifts, and maybe more so than we ever have. I think that’s a cool thing, because it just continues to further this idea that this show could be more than we thought it could in the beginning.

Bennett Raglin/Getty Images

While we’re on the subject of longevity, do you have an idea of how long this show could last? Would you ever leave it in others’ hands or morph it into something else — or am I just stressing both of you out?

BLICHFELD: No, you’re not stressing us out. Those are definitely questions that are being asked on an ongoing basis, and the answers fluctuate depending on the time of day. [Laughs] What we always come back to is, “Yes, of course the show can continue in all sorts of iterations.” One of the questions we’re asked most consistently is, “So! Weed legalization. What’s going to happen with the Guy?” And it’s like, “Yo, these are just short stories!” It’s not just a weed show. This season, we did try to put the Guy in situations that weren’t just weed deliveries. Maybe he will keep dealing weed, maybe he won’t. The show will be the show.

The premiere has him attending his old dealer’s funeral — that’s certainly not him dealing weed. Why start off there?

BLICHFELD: The idea of doing a story that happens at a wake, we just batted it around for a long time, and then it finally came to fruition as a lot of us are pondering death for some reason. [Laughs] We left off with the Guy last season driving off in his RV, and we wanted to at least pick up the thread of, “Well, then what?” [That] coupled with questions we’re asking about his overall life journey — “What’s next? Is he going to do this forever?” — I think that led to [writing about] a death of somebody that he cared about, a person who was his old dealer. It felt like the right situation to make him a little bit reflective of those questions.

SINCLAIR: Last year we explored the feelings of anxiety a lot, but this year we’re like, “Well yeah, s— is all f—ed up still. What are you going to do? You’re going to die soon, so are you going to enjoy your life or are you going to just be in this anxious prison?”

Right, like, go and hop into an RV and have fun instead!

BLICHFELD: Not only have fun, but also ask the greater questions about, what’s meaningful? What matters to me?

SINCLAIR: There are things greater than what’s in the news that are worth paying attention to. Bigger questions worth answering than, collusion or no?

Speaking of politics, though, the second episode does feature “Bronx Obama.” How did you find out about him and get him to be on the show?

SINCLAIR: We were with some writers on a writing assignment and we looked over and we thought we saw Barack Obama driving a cab. One of my writers was like, “Did you see that?” And I was like, “Yeah, I did!” It was kind of a placeholder for a little while. We never thought we’d be able to use it, and then…I’m really glad we stuck to our guns on that one.